You can take PM while you menstruate... I would just not recommend taking it within the first two days of your menstruation (Chiyomilk did this to avoid worsening cramping and to avoid overdosing).
If your testosterone is on the low end of normal, I would not bother with it at all. The point is not to completely get rid of testosterone, as it is a healthy balance that actually is the key to breast growth.
As for the borage oil with PM-- meh, it is fine. PM is a phytoestrogen, while borage oil merely raises aromatase. They will not interfere with one another. Check this out: http://beboard.proboards.com/thread/1051
There is no difference in what order you take of what you have listed above.